Template-Directed Synthesis of Shape-Persistent Macrocyclic Amphiphiles with Convergently Arranged Functionalities

✍ Scribed by Sigurd Höger; Anne-Désirée Meckenstock

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 134 KB
• Volume: 5
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/(sici)1521-3765(19990604)5:6<1686::aid-chem1686>3.0.co;2-0

✦ Synopsis

The template-directed synthesis of shape-persistent macrocyclic amphiphiles is described. Two macrocycles with convergently arranged functional groups (hydroxyl and carboxylic acids) are prepared by intramolecular Glaser coupling of the appropriate templated tetraacetylenes. These structures are formed by the quadruple Hagihara coupling of monoprotected bisacetylenes to appropriate tetraiodides and subsequent desilylation, resulting in a rapid increase of complexity of the intermediates as well as easy formation of structures with different convergent functional groups.